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Assessment of the Maillard reaction of fructose and lysine by analysis of 2-furoylmethyl-amino acids

AutorCastillo, M. Dolores del ; Silván, José Manuel ; Amigo-Benavent, Miryam; Moreno, F. Javier ; Olano, Agustín
Fecha de publicación2006
CitaciónIV Workshop Cost Action 927-IMARS (2006)
Resumenlysine and arginine. This reaction is relevant both in food science and biology. Since aldose reducing sugar such as glucose and lactose are major carbonyl compounds in biology and food, there has been considerable interest in studying their glycation products. Particular attention has been dedicated to the initial glycation product from the reaction of aldose and lysine, also known as Amadori products. Less information related to the condensation products of ketose such as fructose with lysine leading to glucoselysine also called Heyns product is available. The aim of the present research was to evaluate the usefulness of the analysis of the type-Heyns products of lysine with fructose and fructans as 2-furoylmethyl amino acids, which are widely employed for the indirect measurement of Amadori compounds. Model systems of e-amino-lysine and ketose (fructose and fructans (DP 2-8) in methanol were heated under reflux until pale yellow colour was developed. Formation of Heyns compounds were detected by electrospray ionisation-mass spectrometry (ESI-MS). Samples were thermal digested with 8M HCL to obtain the corresponding 2-furoylmethyl amino acid (2-FM-AA) and analysed by ion-pair RP-HPLC. The identity of Heyns compounds was also confirmed by RP-HPLC-MS analysis of their 2-FM-AA. Analysis by ESI-MS showed the presence of the ions (M + H)+ 309.2 and 471.3 due to the Heyns compounds mono-fructosyl-Lys and di-fructosyl-Lys, respectively. Glycation products of lysine with fructose and fructans were observed by RP-HPLC in the studied samples. Also Heyns products of soy proteins with these sugars have been measured following this analysis. In agreement, it can be concluded that ion-pair RP-HPLC is adequate to trace Heyns compounds. Further investigations should be conducted to compare the yield of formation of 2-furoylmethyl amino acids derivatives from Heyns and Amadori products.
DescripciónResumen del póster presentado al IV Workshop Cost Action 927-IMARS: The Maillard Reaction in Food and Medicine, celebrado en Napoles (Italia) del 24 al 27 de mayo de 2006.
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